The purpose of the Synchronous Interactive Video Conference Distance Learning pilot program was to use emerging technologies to expand learning opportunities for students at an urban public high school. Through grant funding, students were able to enroll in Advanced Placement and foreign language courses through an online learning provider. Using case study methodology, the pilot program was thoroughly examined through the analysis of multiple sources of data such as surveys of multiple stakeholders, interviews of program administrators, and the examination of student course documentation. The attrition rate was high at 61.9%. The combination of insufficient time for planning and preparation, lack of support for students, and poor communication was detrimental to the program.